2-Aminopyrimidine-5-boronic acid, pinacol ester → HCID 24947412, compound

HRID 881271Notes

Reaction equation

HRID 881271 reaction equation
[CH3:1][N:2]([CH3:29])[C:3]([N:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[S:20][C:19]3[C:18]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[N:17][C:16](Cl)=[N:15][C:14]=3[C:13]=2[CH3:28])[CH2:7][CH2:6]1)=[O:4].CC1(C)C(C)(C)OB([C:38]2[CH:39]=[N:40][C:41]([NH2:44])=[N:42][CH:43]=2)O1>>[NH2:44][C:41]1[N:42]=[CH:43][C:38]([C:16]2[N:17]=[C:18]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[C:19]3[S:20][C:12]([CH2:11][N:8]4[CH2:9][CH2:10][N:5]([C:3]([N:2]([CH3:29])[CH3:1])=[O:4])[CH2:6][CH2:7]4)=[C:13]([CH3:28])[C:14]=3[N:15]=2)=[CH:39][N:40]=1

Participants

3

Reactant 2

HCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 86623516HCID 86623516, compound

Product 1

HCID 24947412HCID 24947412, compound

Procedure

4-(2-Chloro-7-methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-piperazine-1-carboxylic acid dimethylamide was reacted with 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrimidin-2-ylamine in General Procedure A. Purification on silica yielded 126. NMR (CDCl3): 2.44 (s, 3H, CH3), 2.56-2.60 (m, 4H, 2×CH2), 2.85 (s, 6H, 2×CH3), 3.31-3.33 (m, 4H, 2×CH2), 3.83 (s, 2H, CH2), 3.88-3.91 (m, 4H, 2×CH2), 4.03-4.05 (m, 4H, 2×CH2), 5.22 (sbr, 2H, NH2), 9.35 (s, 2H, 2×ArH). MS: (ESI+): MH+=498.32

Workup

  1. customPurification on silica

Sources & evidence

ORD record
ord-c84b54a09a094fa48a47ca7947c2e4ca
Source dataset
uspto-grants-2015_03
Patent number
US08993563B2

Reaction notes

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